CA2685310A1 - Crystalline and pure modafinil, and process of preparing the same - Google Patents
Crystalline and pure modafinil, and process of preparing the same Download PDFInfo
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- CA2685310A1 CA2685310A1 CA002685310A CA2685310A CA2685310A1 CA 2685310 A1 CA2685310 A1 CA 2685310A1 CA 002685310 A CA002685310 A CA 002685310A CA 2685310 A CA2685310 A CA 2685310A CA 2685310 A1 CA2685310 A1 CA 2685310A1
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- modafinil
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- theta
- crystalline
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- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 title claims abstract 82
- 229960001165 modafinil Drugs 0.000 title claims abstract 65
- 238000000034 method Methods 0.000 title claims abstract 4
- 238000004519 manufacturing process Methods 0.000 claims abstract 12
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
- 239000007788 liquid Substances 0.000 claims 20
- 239000000203 mixture Substances 0.000 claims 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 7
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 239000002552 dosage form Substances 0.000 claims 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 claims 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
- C30B29/54—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Metallurgy (AREA)
- Materials Engineering (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Laminated Bodies (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Glass Compositions (AREA)
Abstract
The present invention provides an improved process for preparing modafinil, whereby it may be isolated in high purity by a single crystallization. The process produces modafinil free of sulphone products of over-oxidation and other byproducts. The invention further provides new crystalline Forms II-VI of modafinil and processes for preparing them. Each of the new forms is differentiated by a unique powder X-ray diffraction pattern. The invention further provides pharmaceutical compositions containing novel modafinil Forms II-IV and VI.
Claims (41)
1. A process for preparing modafinil Form I comprising the steps of:
a) dissolving modafinil in a liquid selected from the group consisting of acetone, acetonitrile, benzyl alcohol, dimethyl formamide, methanol, methyl ethyl ketone, pyrrolidone and mixtures thereof, b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain modafinil Form I.
a) dissolving modafinil in a liquid selected from the group consisting of acetone, acetonitrile, benzyl alcohol, dimethyl formamide, methanol, methyl ethyl ketone, pyrrolidone and mixtures thereof, b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain modafinil Form I.
2. The process of claim 1 wherein the liquid is methanol or acetone.
3. A process for preparing modafinil Form I comprising the steps of:
a) suspending modafinil in ethyl acetate for a period of time sufficient to convert it into modafinil Form I, and b) separating the ethyl acetate to obtain modafinil Form I.
a) suspending modafinil in ethyl acetate for a period of time sufficient to convert it into modafinil Form I, and b) separating the ethyl acetate to obtain modafinil Form I.
4. A process for preparing modafinil Form I comprising the steps of:
a) suspending crystalline Form II modafinil in a liquid selected from the group consisting of methyl t-butyl ether, water, isobutyl acetate and mixtures thereof for a period of time sufficient to convert the Form II modafinil into modafinil Form I, and b) separating the liquid to obtain modafinil Form I.
a) suspending crystalline Form II modafinil in a liquid selected from the group consisting of methyl t-butyl ether, water, isobutyl acetate and mixtures thereof for a period of time sufficient to convert the Form II modafinil into modafinil Form I, and b) separating the liquid to obtain modafinil Form I.
5. A process for preparing modafinil Form I by heating Form V modafinil to about 80°C or higher temperature for a period of time sufficient to convert the Form V modafinil into Form I modafinil.
6. A process for preparing modafinil Form I by heating Form VI modafinil to about 80°C or higher temperature for a period of time sufficient to convert the Form V modafinil into modafinil Form I.
7. A crystalline form of modafinil that produces a powder X-ray diffraction pattern with reflections at 14.3, 17.5, 20.5 and 21.3~0.2 degrees 2.theta..
8. The crystalline modafinil of claim 7 denominated modafinil Form II.
9. The crystalline form of modafinil of claim 7 wherein the reflections at 14.3, 17.5, 20.5 and 21.3~0.2 degrees 20 comprise a first set of reflections of strong intensity and wherein the crystalline form is further characterized by reflections of lesser intensity at 9.1,
10.3, 11.9, 15.2, 18.4, 24.6 and 26.6~0.2 degrees 2.theta..
10. The crystalline form of modafinil of claim 7 that produces a powder X-ray diffraction pattern with reflections at 9.1, 10.3, 11.1, 11.9, 14.3, 15.2, 16.4, 17.5, 18.4, 20.5, 21.3, 24.6, 26.6~0.2 degrees 2.theta..
10. The crystalline form of modafinil of claim 7 that produces a powder X-ray diffraction pattern with reflections at 9.1, 10.3, 11.1, 11.9, 14.3, 15.2, 16.4, 17.5, 18.4, 20.5, 21.3, 24.6, 26.6~0.2 degrees 2.theta..
11. A process for preparing the modafinil of claim 7 comprising the steps of:
a) suspending Form III modafinil in water for a period of time sufficient to convert Form III modafinil into the modafinil of claim 7, and b) separating the water to obtain the modafinil of claim 7.
a) suspending Form III modafinil in water for a period of time sufficient to convert Form III modafinil into the modafinil of claim 7, and b) separating the water to obtain the modafinil of claim 7.
12. A process for preparing the modafinil of claim 7 comprising the steps of:
a) dissolving modafinil in a liquid selected from the group consisting of ethanol, isopropanol, n-butanol, t-butanol, methyl isobutyl ketone, ethylene glycol, dioxolane, dioxane and mixtures thereof, b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain the modafinil of claim 7.
a) dissolving modafinil in a liquid selected from the group consisting of ethanol, isopropanol, n-butanol, t-butanol, methyl isobutyl ketone, ethylene glycol, dioxolane, dioxane and mixtures thereof, b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain the modafinil of claim 7.
13. A crystalline form of modafinil that produces a powder X-ray diffraction pattern with reflections at 7.4, 10.5, 20.0 and 20.5~0.2 degrees 2.theta..
14. The crystalline modafinil of claim 13 denominated modafinil Form III.
15. The crystalline form of modafinil of claim 13 wherein the reflections at 7.4, 10.5, 20.0 and 20.5~0.2 degrees 2.theta. comprise a first set of reflections of strong intensity and wherein the crystalline form is further characterized by reflections of lesser intensity at 9.0, 12.3, 22.1 and 24.5~0.2 degrees 2.theta..
16. The crystalline form of modafinil of claim 15 that produces a powder X-ray diffraction pattern with reflections at 7.4, 9.0, 10.5, 12.3, 14.2, 14.7, 15.1, 16.4, 18.3, 20.0, 20.5, 21.1, 22.1, 24.5~0.2 degrees 2.theta..
17. A process for preparing the modafinil of claim 13 comprising the steps of:
a) dissolving modafinil in a liquid selected from the group consisting of toluene and mixtures of ethanol and dimethylcarbonate, b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain the modafinil of claim 13.
a) dissolving modafinil in a liquid selected from the group consisting of toluene and mixtures of ethanol and dimethylcarbonate, b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain the modafinil of claim 13.
18. A crystalline form of modafinil that produces a powder X-ray diffraction pattern with reflections at 6.9, 10.4, 17.2, 20.3 and 22.7~0.2 degrees 2.theta..
19. The crystalline modafinil of claim 18 denominated modafinil Form IV.
20. The crystalline form of modafinil of claim 18 wherein the reflections at 6.9, 10.4, 17.2, 20.3 and 22.7~0.2 degrees 2.theta. comprise a first set of reflections of strong intensity and wherein the crystalline form is further characterized by reflections of lesser intensity at 14.1, 18.5, 20.8, 21.6 and 25.0~0.2 degrees 2.theta..
21. The crystalline form of modafinil of claim 20 that produces a powder X-ray diffraction pattern with reflections at 6.9, 10.4, 14.1, 17.2, 18.5, 20.3, 20.8, 21.6, 22.7, 25.0, 26.5, 27.6, 28.5~0.2 degrees 2.theta..
22. A process for preparing the modafinil of claim 18 comprising the steps of:
a) dissolving modafinil in a liquid selected from the group consisting of tetrahydrofuran and dimethyl sulfoxide b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain the modafinil of claim 18.
a) dissolving modafinil in a liquid selected from the group consisting of tetrahydrofuran and dimethyl sulfoxide b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain the modafinil of claim 18.
23. A crystalline hemisolvate of modafinil and dimethylcarbonate.
24. The crystalline hemisolvate of modafinil and dimethylcarbonate of claim 23 that produces a powder X-ray diffraction pattern with reflections at 9.3, 12.4, 18.2, 19.9 and 22.0~0.2 degrees 2.theta..
25. The crystalline hemisolvate of modafinil and dimethylcarbonate of claim 23 denominated modafinil Form V.
26. The crystalline form of modafinil of claim 24 wherein the reflections at 9.3, 12.4, 18.2, 19.9 and 22.0~0.2 degrees 2.theta. comprise a first set of reflections of strong intensity and wherein the crystalline form is further characterized by reflections of lesser intensity at 7.4, 24.7, 26.2, 21.5, 23.6, 24.5 and 25.2~0.2 degrees 2.theta..
27. The crystalline form of modafinil of claim 26 that produces a powder X-ray diffraction pattern with reflections at 7.4, 9.3, 10.5, 12.4, 14.7, 16.2, 18.2, 19.9, 21.5, 22.0, 23.6, 24.5, 25.2, 28.4, 29.5, 31.8~0.2 degrees 2.theta..
28. A process for preparing the modafinil of claim 23 comprising the steps of:
a) dissolving modafinil in liquid selected from the group consisting of methylcarbonate, ethanol and dimethylcarbonate mixtures, water and dimethylcarbonate mixtures and acetone and dimethylcarbonate mixtures, b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain the modafinil of claim 23.
a) dissolving modafinil in liquid selected from the group consisting of methylcarbonate, ethanol and dimethylcarbonate mixtures, water and dimethylcarbonate mixtures and acetone and dimethylcarbonate mixtures, b) crystallizing modafinil from the liquid, and c) separating the liquid to obtain the modafinil of claim 23.
29. A crystalline form of modafinil that produces a powder X-ray diffraction pattern with reflections at 9.3, 18.2, and 20.5~0.2 degrees 2.theta..
30. The crystalline modafinil of claim 29 denominated modafinil Form VI.
31. The crystalline form of modafinil of claim 29 wherein the reflections at 9.3, 18.2, and 20.5~0.2 degrees 2.theta. comprise a first set of reflections of strong intensity and wherein the crystalline form is further characterized by reflections of lesser intensity at 9.0, 10.2, 12.4, 15.3, and 20.0~0.2 degrees 2.theta..
32. The crystalline form of modafinil of claim 31 that produces a powder X-ray diffraction pattern with reflections at 9.0, 9.3, 10.2, 12.4, 14.2, 14.5, 15.3, 17.5, 18.1, 20.0, 20.5, 21.5, 22.0, 23.5, 24.5, 25.0~0.2 degrees 2.theta..
33. A process for preparing the modafinil of claim 29 comprising the steps of:
a) suspending Form V modafinil in a liquid selected from the group consisting of water, ethanol and ethanol and water mixtures for a period of time sufficient to convert the Form V modafinil into the modafinil of claim 29, and b) separating the liquid to obtain the modafinil of claim 29.
a) suspending Form V modafinil in a liquid selected from the group consisting of water, ethanol and ethanol and water mixtures for a period of time sufficient to convert the Form V modafinil into the modafinil of claim 29, and b) separating the liquid to obtain the modafinil of claim 29.
34. A pharmaceutical composition comprising the modafinil of claim 7 and a pharma-ceutically acceptable excipient.
35. A pharmaceutical dosage form comprising the composition of claim 34.
36. A pharmaceutical composition comprising the modafinil of claim 13 and a pharma-ceutically acceptable excipient.
37. A pharmaceutical dosage form comprising the composition of claim 36.
38. A pharmaceutical composition comprising the modafinil of claim 18 and a pharma-ceutically acceptable excipient.
39. A pharmaceutical dosage form comprising the composition of claim 38.
40. A pharmaceutical composition comprising the modafinil of claim 29 and a pharma-ceutically acceptable excipient.
41. A pharmaceutical dosage form comprising the composition of claim 40.
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22111000P | 2000-07-27 | 2000-07-27 | |
| US60/221,110 | 2000-07-27 | ||
| US22649100P | 2000-08-18 | 2000-08-18 | |
| US60/226,491 | 2000-08-18 | ||
| US22916000P | 2000-08-30 | 2000-08-30 | |
| US60/229,160 | 2000-08-30 | ||
| US23008800P | 2000-09-05 | 2000-09-05 | |
| US60/230,088 | 2000-09-05 | ||
| US25933201P | 2001-01-02 | 2001-01-02 | |
| US60/259,332 | 2001-01-02 | ||
| CA2416792A CA2416792C (en) | 2000-07-27 | 2001-07-27 | Crystalline and pure modafinil, and process of preparing the same |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2416792A Division CA2416792C (en) | 2000-07-27 | 2001-07-27 | Crystalline and pure modafinil, and process of preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2685310A1 true CA2685310A1 (en) | 2002-02-07 |
| CA2685310C CA2685310C (en) | 2012-10-16 |
Family
ID=27539819
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2416792A Expired - Fee Related CA2416792C (en) | 2000-07-27 | 2001-07-27 | Crystalline and pure modafinil, and process of preparing the same |
| CA2685310A Expired - Fee Related CA2685310C (en) | 2000-07-27 | 2001-07-27 | Crystalline and pure modafinil, and process of preparing the same |
| CA2634702A Expired - Fee Related CA2634702C (en) | 2000-07-27 | 2001-07-27 | Crystalline and pure modafinil, and process of preparing the same |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2416792A Expired - Fee Related CA2416792C (en) | 2000-07-27 | 2001-07-27 | Crystalline and pure modafinil, and process of preparing the same |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2634702A Expired - Fee Related CA2634702C (en) | 2000-07-27 | 2001-07-27 | Crystalline and pure modafinil, and process of preparing the same |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US6849120B2 (en) |
| EP (3) | EP1309547B1 (en) |
| JP (2) | JP4302977B2 (en) |
| KR (8) | KR100729298B1 (en) |
| CN (2) | CN100500651C (en) |
| AT (1) | ATE453618T1 (en) |
| AU (1) | AU2001283008A1 (en) |
| CA (3) | CA2416792C (en) |
| CY (1) | CY1110234T1 (en) |
| CZ (1) | CZ2003529A3 (en) |
| DE (3) | DE20122504U1 (en) |
| DK (2) | DK1309547T3 (en) |
| ES (2) | ES2277937T3 (en) |
| HR (2) | HRP20030131B1 (en) |
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